Where does my Python output go when I start Blender with a script in Windows?
Git Bash is different from regular terminals, as it tries to bridge the gap in behaviour between UNIX terminals and Windows' console (cmd.exe). Run winpty ./blender.exe to get more immediate output of your print() commands.

Note, however, that winpty seems to mangle filenames, so you have to resort to absolute paths in Windows notation to prevent this.